We recently connected with Rory Lipede and have shared our conversation below.
Rory , so good to have you with us today. We’ve got so much planned, so let’s jump right into it. We live in such a diverse world, and in many ways the world is getting better and more understanding but it’s far from perfect. There are so many times where folks find themselves in rooms or situations where they are the only ones that look like them – that might mean being the only woman of color in the room or the only person who grew up in a certain environment etc. Can you talk to us about how you’ve managed to thrive even in situations where you were the only one in the room?
As a biracial woman, I have often found myself as the only one in the room who looked like me whether as a professional ballet dancer, an entrepreneur, or an advocate for social causes. Rather than seeing this as a disadvantage, I have learned to turn it into a source of strength, innovation, and purpose.
I am the founder of Telltale Tours, a New York City-based company that blends history, literature, nightlife and immersive storytelling to create unforgettable tourism experiences. As a lover of literature, I believe stories have the power to connect people across time and cultures, and that philosophy is deeply woven into my business.
Ultimately, my journey began in the world of ballet, a space where tradition often dictates who belongs. Navigating that world as a biracial dancer required resilience, adaptability, and an unwavering belief in my own abilities. Performing on stage, I learned to command presence, tell a story beyond words, and connect deeply with an audience regardless of background. These same skills became invaluable when I transitioned into entrepreneurship.
What I have learned is this: when you are the only one in the room who looks like you, you have the power to redefine the space. You bring perspectives, ideas, and strengths that others might not have considered. Success comes not from blending in, but from standing out with authenticity and purpose.
By embracing my biracial identity, my love of storytelling, and my passion for ethical and inclusive tourism, I have built a career that is not only fulfilling but also impactful. My advice to anyone in a similar position is simple: own your story, amplify your voice, and create opportunities for others to do the same.
Let’s take a small detour – maybe you can share a bit about yourself before we dive back into some of the other questions we had for you?
My career has always revolved around storytelling. First as a ballet dancer, then as an actor, and now as an entrepreneur. Today, I bring that passion to Telltale Tours, a New York City-based nightlife tour company that offers immersive, after-dark experiences blending history, mystery, and theatrical storytelling.
I have made a conscious effort to set Telltale Tours apart in the nightlife-based, affordable and designed for those who crave a unique, atmospheric way to explore the city after the sun goes down and when eating/drinking alone just isn’t as fun. Whether it’s a historic bar crawl featuring New York’s greats, or a moonlit rooftop exploration of New York’s hidden past, our tours transform the city into a stage where history and storytelling collide. As a performer, I’ve always believed that an engaging story can transport people and that’s exactly what we do on every tour.
But my work isn’t just about entertainment, it’s about impact. Tourism plays a significant role in the global and local economy, but it also has a dark side: human trafficking. Tourism is a global industry where the same networks that bring people together can also enable exploitation. What can bring people together can also be exploited for harmful purposes. That’s why I donate a portion of Telltale Tours’ proceeds to organizations fighting child trafficking, using my platform to raise awareness and contribute to real change.
I’m also developing a program focused on autism-inclusive tourism, with the goal of creating job opportunities for neurodivergent individuals within the hospitality and tourism industries. I believe tourism should be just as accessible as any other experience, and I’m working to ensure that inclusion and affordability is at the core of what we do.
Beyond my work with Telltale Tours, I continue to train and mentor actors and performers, helping them strengthen their craft. Performance and storytelling are at the heart of my work, and I love helping others hone their ability to command an audience and deliver unforgettable experiences.
Looking ahead, I’m focused on expanding Telltale Tours, launching new tours in new cities and continuing to push the boundaries of what nightlife tourism can be. My goal is to not just entertain, but to leave people with an experience they’ll never forget. An experience that sparks curiosity, connection, and conversation.
If you love the thrill of an after-dark adventure, appreciate a great story, or are passionate about ethical and inclusive tourism, I invite you to join one of our tours or collaborate on ways to make an even bigger impact.
Looking back, what do you think were the three qualities, skills, or areas of knowledge that were most impactful in your journey? What advice do you have for folks who are early in their journey in terms of how they can best develop or improve on these?
Looking back on my journey from ballet to acting to entrepreneurship, there are three key qualities and skills that have had the greatest impact on my success: adaptability, storytelling, and purpose-driven leadership. These have shaped not only my career but also the way I approach challenges, opportunities, and the people I serve.
1. Adaptability: The Art of Reinvention
One of the most valuable skills I’ve honed is the ability to adapt and evolve. This may be seen as never being satisfied, I see it as always striving for better. My career has taken me from the highly disciplined world of ballet to the unpredictable stage of acting, and now to the dynamic industry of tourism. Each additional skill required me to learn new skills, embrace change, and step into uncertainty with confidence.
For anyone early in their journey, my advice is this: be open to reinvention. The career path you envision today may shift in unexpected ways. Develop a mindset that sees change as an opportunity rather than a setback. Invest in continuous learning, and don’t be afraid to pivot especially when your passions or circumstances lead you in a new direction.
2. Storytelling: The Power to Connect and Captivate
No matter the industry, storytelling is one of the most powerful tools you can develop. Whether performing on stage, leading a tour, or advocating for a cause, I’ve found that the ability to craft and deliver a compelling story engages, educates, and inspires people in a way that facts alone never could.
For those looking to improve their storytelling skills, my advice is to practice telling stories in everyday life. Start with casual conversations, move onto professional settings, or even writing. Study great storytellers, whether they’re actors, writers, or public speakers. Most importantly, find your unique voice. Ask lots of questions like what personal experiences, perspectives, and ideas make the story worth telling? When you can connect with people emotionally, you can make an unforgettable impact.
3. Purpose-Driven Leadership: Using Business for Good
The most fulfilling part of my journey has been aligning my work with my values. Whether through ethical tourism, supporting anti-trafficking initiatives, or advocating for inclusion in the industry. Leadership isn’t just about achieving success; it’s about making a difference.
For those early in their careers, my advice is to identify what truly matters to you and find ways to integrate it into your work. Whether you’re an entrepreneur, artist, or professional, having a purpose beyond profit will give you resilience during tough times and fulfillment in your successes. Seek out mentors who lead with integrity, and don’t be afraid to champion causes that align with your values.
The intersection of adaptability, storytelling, and purpose-driven leadership has defined my path. If I could offer one key piece of advice to those starting out, it would be this: stay open, stay authentic, and stay committed to work that excites you and serves others. Success isn’t just about where you end up, it’s about the impact you make along the way.
All the wisdom you’ve shared today is sincerely appreciated. Before we go, can you tell us about the main challenge you are currently facing?
The number one challenge I am currently facing is competing with large, corporate-backed booking platforms like GetYourGuide, TripAdvisor and Viator, which take up to 40% of ticket sales from small, local businesses like mine. These platforms dominate search results and control much of the tourism industry, making it difficult for boutique operators to stand out, sustain, and grow. Telltale Tours is all about providing an intimate, immersive nightlife experience that supports local bars, restaurants, and historic sites. However, with such high commission cuts, it’s a constant battle to keep tours affordable while ensuring that my business, my staff and the businesses I partner with see meaningful financial benefits.
How I’m Overcoming This Challenge:
1. Encouraging Direct Bookings & Educating Travelers
I actively encourage guests to book directly through our website when they return and educate them about the impact of third-party booking platforms. Many travelers don’t realize how much these platforms take from small businesses.
2. Building a Stronger Brand & Community Presence
Instead of relying solely on major booking sites, I focus on organic marketing, local partnerships, and word-of-mouth referrals. By collaborating with bars, event spaces, and influencers, we create experiences that go beyond just a tour—they’re part of the fabric of the city.
3. Using PR & Media to Establish Expertise
Another major challenge is being heard and seen as an expert in a space where people don’t typically expect a squeaky-voiced, bi-racial, 5’2” activist to be leading a history tour company. It’s an industry where traditional (and often outdated) voices dominate, so I actively work to change that. I’ve been seeking press coverage, podcast interviews, and speaking engagements to help establish myself in the industry. It is a marathon I happily walk.
4. Investing in Customer Experience & Reviews
Since big platforms dominate search engines, I put a strong focus on creating an unforgettable experience that leads to organic word-of-mouth growth. A well-told story, a perfectly curated speakeasy stop, or a fascinating untold piece of history can leave a lasting impression and when people talk about our tours, leave great reviews, and refer friends, it helps us grow independently from the big platforms.
5. Leveraging Digital Marketing & SEO
Since we can’t outspend big companies in advertising, I focus on SEO (search engine optimization), targeted social media campaigns, and engaging the concierge world to drive traffic to our website. I want people searching for history, drinking, and nightlife tours in New York City to find Telltale Tours first, rather than being funneled into a generic experience.
Why I Keep Going:
Even with these challenges, I love what I do. There’s something special about bringing history to life, making people laugh and creating unforgettable moments. Knowing that my tours help support, entertainers, local businesses and amplify diverse voices in storytelling makes it all worth it. I’ll continue to fight for independent, high-quality tourism experiences and to remind people that supporting local matters.
If you’re reading this and love unique, small-business-driven experiences, book directly, support local, and seek out the storytellers who bring a city to life!
Contact Info:
- Website: Telltale Tours
- Instagram: @telltaletours
- Facebook: https://www.facebook.com/share/1F5QhQBW5y/?mibextid=wwXIfr
- Linkedin: https://www.linkedin.com/in/rory-lipede-792ab3ab
- Twitter: https://x.com/telltaletour?s=21&t=LpC1K7ktvlW8LHSkzSZ0CA
- Youtube: https://yelp.to/wtvHYwTK2H
- Yelp: https://yelp.to/wtvHYwTK2H
- Other:
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